3,4-dihydro-2H-pyran → 2-(Oxan-2-yloxy)isoindole-1,3-dione

HRID 874519ノート

反応式

HRID 874519 の反応式
[OH:1][N:2]1[C:6](=[O:7])[C:5]2=[CH:8][CH:9]=[CH:10][CH:11]=[C:4]2[C:3]1=[O:12].[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C(Cl)Cl.O1CCOCC1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH:14]1[O:1][N:2]1[C:3](=[O:12])[C:4]2[C:5](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:7]

参加物

6

反応物 2

HCID 80803,4-dihydro-2H-pyranHCID 10665N-Hydroxyphthalimide

生成物 1

HCID 2895872-(Oxan-2-yloxy)isoindole-1,3-dione収率 88.3%

試薬・触媒・溶媒 3

HCID 6101p-Toluenesulfonic acid触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

to a vigorously stirred solution of N-hydroxyphthalimide (10.0 g, 61.4 mmol) in CH2Cl2 (70 mL) and dioxane (80 mL) was added dihydropyran (6.16 mL, 67.6 mmol) and p-toluenesulfonic acid (200 mg). The resulting solution was stirred overnight at room temperature. The reaction was quenched by slow addition of saturated NaHCO3 (100 mL). After separation, the organic layer was washed with brine and dried over Na2SO4. Solvent removal under vacuum yielded 13.4 g (88%) of 2-(tetrahydro-2H-pyran-2-yloxy)isoindoline-1,3-dione as a white solid.

後処理

  1. customThe reaction was quenched by slow addition of saturated NaHCO3 (100 mL)
  2. customAfter separation
  3. washthe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customSolvent removal under vacuum

出典と根拠

ORDレコード
ord-13cb4623d1bd43ea94c508923fd50c3a
出典データセット
uspto-grants-2015_03
特許番号
US08980909B2

反応ノート

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